Unusual Rearrangement by Anodic Oxidation of Cycloalkanones in the Presence of Trifluoroacetic Acid
Anodic oxidation of cyclopentanone and cyclohexanones in a mixed solvent of CF3COOH and CH2C12 containing triethylamine led to unusual rearrangement to give selectively γ-valerolactone and a mixture of γ-and δ-lactones, respectively.
Anodic cleavage of a bond between the carbonyl carbon and the adjacent carbon of cycloalkanones followed by Wagner-Meerwein rearrangement and re-cyclization may be proposed as one of the most plausible reaction mechanisms.
KeywordsAnodic Oxidation Carbonyl Carbon Lithium Perchlorate Sole Product Cyclic Ketone
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